Scutaro certainly makes sense for Boston; he's the best available shortstop, considering both the free agent and trade market. We ranked Scutaro the eighth-best free agent overall, perhaps a reflection of a weaker market this year. It'd be nice to see Scutaro sign with the Red Sox, as we'd get at least one of our 50 predictions right.

Aside from committing a multiyear contract to Scutaro, the Sox might have to surrender their #29 pick in the June 2010 draft to the Blue Jays. Looking at the Elias numbers, it is possible that the Jays get screwed out of a first-rounder again, as they did losing A.J. Burnett last year (of course, the Jays failed to sign James Paxton anyway). If the Red Sox sign Scutaro and any of Soriano, Gonzalez, Holliday, or Lackey, the Braves, Cardinals, or Angels would get Boston's #29 pick instead and the Jays would get their second-rounder (assuming arbitration is offered to those players).

As Silverman notes, Escobar would fit right in with the John Smoltz/Brad Penny signings of last year. Those two bombed, but here's the question – what kind of success rate should the Red Sox expect from these one-year pitcher gambles? It is OK if one out of five works out?